(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

Base Information

Chemical Name:(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol
CAS No.:914638-79-2
Molecular Formula:C₄₈H₅₆O₆Si
Molecular Weight:757.055
Hs Code.:

Synonyms:(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

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Chemical Property of (3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

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Technology Process of (3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

There total 14 articles about (3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

: 914638-66-7
1-((1R,3S)-3-Benzyloxy-1-methyl-pent-4-ynyloxymethyl)-4-methoxy-benzene

: 914638-64-5
(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanal

: 914638-79-2
(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-92-9
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-en-1-ol

: 914638-79-2
(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

2.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

2.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

3.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

5.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

6.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

7.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

8.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

With titanium(IV) isopropylate; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; Cumene hydroperoxide; camphor-10-sulfonic acid; sodium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-72-5
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-enoic acid ethyl ester

: 914638-79-2
(3S,7S,9R)-3,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-yn-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 65 percent / LiAlH₄; AlCl₃ / diethyl ether / 6 h / 0 °C

2.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

3.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

3.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

4.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

6.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

7.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

9.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

With titanium(IV) isopropylate; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; Cumene hydroperoxide; camphor-10-sulfonic acid; sodium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.08.035